NL7907985A - Tetrahydroxanthon derivaten. - Google Patents
Tetrahydroxanthon derivaten. Download PDFInfo
- Publication number
- NL7907985A NL7907985A NL7907985A NL7907985A NL7907985A NL 7907985 A NL7907985 A NL 7907985A NL 7907985 A NL7907985 A NL 7907985A NL 7907985 A NL7907985 A NL 7907985A NL 7907985 A NL7907985 A NL 7907985A
- Authority
- NL
- Netherlands
- Prior art keywords
- hydrogen
- group
- short chain
- formula
- chain alkyl
- Prior art date
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- OPRFTHPXVIXGNH-UHFFFAOYSA-N 1,2,3,4-tetrahydroxanthen-9-one Chemical class O1C2=CC=CC=C2C(=O)C2=C1CCCC2 OPRFTHPXVIXGNH-UHFFFAOYSA-N 0.000 title claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 20
- 150000002431 hydrogen Chemical group 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- -1 cyano, carboxy Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004423 acyloxy group Chemical group 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 101150041968 CDC13 gene Proteins 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229960001340 histamine Drugs 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- VSGGERJSQCCMBD-UHFFFAOYSA-N 9-oxo-5,6,7,8-tetrahydroxanthene-2-carbonitrile Chemical compound O1C2=CC=C(C#N)C=C2C(=O)C2=C1CCCC2 VSGGERJSQCCMBD-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 108091029430 CpG site Proteins 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- DNZIRCDMTRDBLU-UHFFFAOYSA-N 7-bromo-1,2,3,4-tetrahydroxanthen-9-one Chemical compound C1CCCC2=C1OC1=CC=C(Br)C=C1C2=O DNZIRCDMTRDBLU-UHFFFAOYSA-N 0.000 description 3
- DROUHTGBXFUQKP-UHFFFAOYSA-N 7-bromo-2-hydroxy-1,2,3,4-tetrahydroxanthen-9-one Chemical compound O1C2=CC=C(Br)C=C2C(=O)C2=C1CCC(O)C2 DROUHTGBXFUQKP-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000012453 sprague-dawley rat model Methods 0.000 description 3
- VIYZWWOPKHUZQS-UHFFFAOYSA-N (7-bromo-9-oxo-1,2,3,4-tetrahydroxanthen-2-yl) acetate Chemical compound O1C2=CC=C(Br)C=C2C(=O)C2=C1CCC(OC(=O)C)C2 VIYZWWOPKHUZQS-UHFFFAOYSA-N 0.000 description 2
- RWNLIKKFPRLEQW-UHFFFAOYSA-N 6-methyl-9-oxo-1,2,3,4-tetrahydroxanthene-2-carbonitrile Chemical compound C1CC(C#N)CC2=C1OC1=CC(C)=CC=C1C2=O RWNLIKKFPRLEQW-UHFFFAOYSA-N 0.000 description 2
- LHJLAOLAINQYMV-UHFFFAOYSA-N 7-bromo-2-methoxy-1,2,3,4-tetrahydroxanthen-9-one Chemical compound O1C2=CC=C(Br)C=C2C(=O)C2=C1CCC(OC)C2 LHJLAOLAINQYMV-UHFFFAOYSA-N 0.000 description 2
- PIRKKCGJNJZIFE-UHFFFAOYSA-N 9-oxo-5,6,7,8-tetrahydroxanthene-2-carboxylic acid Chemical compound C1CCCC2=C1OC1=CC=C(C(=O)O)C=C1C2=O PIRKKCGJNJZIFE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010002198 Anaphylactic reaction Diseases 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VCAQPYXOWLIOSF-UHFFFAOYSA-N acetic acid;sulfuric acid;hydrate Chemical compound O.CC(O)=O.OS(O)(=O)=O VCAQPYXOWLIOSF-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 230000036783 anaphylactic response Effects 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- 230000003266 anti-allergic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- 229960000265 cromoglicic acid Drugs 0.000 description 2
- IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 2
- 238000007333 cyanation reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 210000003200 peritoneal cavity Anatomy 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KTZNVZJECQAMBV-UHFFFAOYSA-N 1-(cyclohexen-1-yl)pyrrolidine Chemical compound C1CCCN1C1=CCCCC1 KTZNVZJECQAMBV-UHFFFAOYSA-N 0.000 description 1
- NNEOYCMCJMLRSD-UHFFFAOYSA-N 1-benzyl-4-bromobenzene Chemical compound C1=CC(Br)=CC=C1CC1=CC=CC=C1 NNEOYCMCJMLRSD-UHFFFAOYSA-N 0.000 description 1
- ABEXEQSGABRUHS-UHFFFAOYSA-N 16-methylheptadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C ABEXEQSGABRUHS-UHFFFAOYSA-N 0.000 description 1
- LRVGGQMEAXZANS-UHFFFAOYSA-N 2-[(9-oxo-5,6,7,8-tetrahydroxanthene-2-carbonyl)amino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC(=O)C1=CC=C(OC2=C(CCCC2)C2=O)C2=C1 LRVGGQMEAXZANS-UHFFFAOYSA-N 0.000 description 1
- VRJBEVQGJOSGOX-UHFFFAOYSA-N 2-acetyloxy-5-bromobenzoic acid Chemical compound CC(=O)OC1=CC=C(Br)C=C1C(O)=O VRJBEVQGJOSGOX-UHFFFAOYSA-N 0.000 description 1
- OAEAAENUMGYEJL-UHFFFAOYSA-N 6-methyl-9-oxo-1,2,3,4-tetrahydroxanthene-2-carboxamide Chemical compound C1CC(C(N)=O)CC2=C1OC1=CC(C)=CC=C1C2=O OAEAAENUMGYEJL-UHFFFAOYSA-N 0.000 description 1
- JGYDVTDZIVCXQJ-UHFFFAOYSA-N 9-oxo-1,2,3,4-tetrahydroxanthene-2-carboxylic acid Chemical compound O1C2=CC=CC=C2C(=O)C2=C1CCC(C(=O)O)C2 JGYDVTDZIVCXQJ-UHFFFAOYSA-N 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- 208000019300 CLIPPERS Diseases 0.000 description 1
- 101100279436 Caenorhabditis elegans egg-2 gene Proteins 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 241000764238 Isis Species 0.000 description 1
- 101001116283 Phanerodontia chrysosporium Manganese peroxidase H4 Proteins 0.000 description 1
- 101001018261 Protopolybia exigua Mastoparan-1 Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 208000021930 chronic lymphocytic inflammation with pontine perivascular enhancement responsive to steroids Diseases 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000005417 image-selected in vivo spectroscopy Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000012739 integrated shape imaging system Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940092253 ovalbumin Drugs 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- NAHBVNMACPIHAH-HLICZWCASA-N p-ii Chemical compound C([C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H]2CSSC[C@H](NC(=O)[C@H](CC=3C=CC=CC=3)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC2=O)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(N)=O)=O)C(C)C)C1=CC=CC=C1 NAHBVNMACPIHAH-HLICZWCASA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000009951 qiqi Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13495878 | 1978-11-01 | ||
| JP13495878A JPS5562082A (en) | 1978-11-01 | 1978-11-01 | Tetrahydroxanthone derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL7907985A true NL7907985A (nl) | 1980-05-06 |
Family
ID=15140544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL7907985A NL7907985A (nl) | 1978-11-01 | 1979-10-31 | Tetrahydroxanthon derivaten. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4290954A (enrdf_load_stackoverflow) |
| JP (1) | JPS5562082A (enrdf_load_stackoverflow) |
| DE (1) | DE2944413A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2440951A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2039475B (enrdf_load_stackoverflow) |
| IT (1) | IT1165719B (enrdf_load_stackoverflow) |
| NL (1) | NL7907985A (enrdf_load_stackoverflow) |
| SE (1) | SE445916B (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4571405A (en) * | 1984-05-29 | 1986-02-18 | Miles Laboratories, Inc. | Anti-allergic chromone- or thiochromone-5-oxamic acid derivatives, compositions, and method of use therefor |
| US5977077A (en) * | 1995-08-28 | 1999-11-02 | Interlab Corporation | Xanthone analogs for the treatment of infectious diseases |
| US6613797B2 (en) | 1999-12-02 | 2003-09-02 | Interlab, Inc. | Xanthone analogs for treating infectious diseases and complexation of heme and porphyrins |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4061768A (en) * | 1971-09-08 | 1977-12-06 | Burroughs Wellcome Co. | Certain cyclic carbonyl compounds used in the prophylaxis of allergic conditions |
| US4127573A (en) * | 1972-09-06 | 1978-11-28 | Burroughs Wellcome Co. | Ditetrazole substituted acridone compounds |
| US3862141A (en) * | 1973-08-23 | 1975-01-21 | Warner Lambert Co | 1-substituted 1,2,3,4-tetrahydroxanthen-9-ones |
| US4078078A (en) * | 1974-07-09 | 1978-03-07 | Roussel Uclaf | Novel xanthone-2-carboxylic acid compounds |
| JPS5229677A (en) * | 1975-09-02 | 1977-03-05 | Ishikawajima Harima Heavy Ind Co Ltd | Dust collecting device |
| JPS6024106B2 (ja) * | 1975-09-22 | 1985-06-11 | 興和株式会社 | キサンテン誘導体の製法 |
| JPS6034551B2 (ja) * | 1977-02-07 | 1985-08-09 | 興和株式会社 | テトラヒドロキサントン誘導体 |
| US4221800A (en) * | 1977-12-23 | 1980-09-09 | Miles Laboratories, Inc. | Cycloalkenochromone |
-
1978
- 1978-11-01 JP JP13495878A patent/JPS5562082A/ja active Granted
-
1979
- 1979-10-30 US US06/089,403 patent/US4290954A/en not_active Expired - Lifetime
- 1979-10-31 SE SE7909031A patent/SE445916B/sv not_active IP Right Cessation
- 1979-10-31 FR FR7927087A patent/FR2440951A1/fr active Granted
- 1979-10-31 NL NL7907985A patent/NL7907985A/nl not_active Application Discontinuation
- 1979-10-31 GB GB7937654A patent/GB2039475B/en not_active Expired
- 1979-11-01 DE DE19792944413 patent/DE2944413A1/de not_active Ceased
- 1979-11-02 IT IT69141/79A patent/IT1165719B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| US4290954A (en) | 1981-09-22 |
| FR2440951B1 (enrdf_load_stackoverflow) | 1983-04-01 |
| IT7969141A0 (it) | 1979-11-02 |
| SE7909031L (sv) | 1980-05-02 |
| SE445916B (sv) | 1986-07-28 |
| DE2944413A1 (de) | 1980-08-07 |
| JPS6148513B2 (enrdf_load_stackoverflow) | 1986-10-24 |
| GB2039475B (en) | 1982-09-22 |
| GB2039475A (en) | 1980-08-13 |
| JPS5562082A (en) | 1980-05-10 |
| FR2440951A1 (fr) | 1980-06-06 |
| IT1165719B (it) | 1987-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |